CN1026113C - 烷基苷的制备方法 - Google Patents

烷基苷的制备方法 Download PDF

Info

Publication number: CN1026113C
Authority: CN; China
Prior art keywords: sulfo; acid; alkylglycoside; succinic acid; catalyzer
Prior art date: 1989-08-24
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CN90107055.6A

Other languages

English (en)

Chinese (zh)

Other versions

CN1049667A (zh

Inventor

卡尔汉兹·黑尔

曼富莱·温森

汉斯·彼德·考勒

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

A Nice Germany & Co KG GmbH

Original Assignee

Henkel AG and Co KGaA

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-08-24

Filing date

1990-08-20

Publication date

1994-10-05

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6387752&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CN1026113(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1990-08-20 Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA

1991-03-06 Publication of CN1049667A publication Critical patent/CN1049667A/zh

1994-10-05 Application granted granted Critical

1994-10-05 Publication of CN1026113C publication Critical patent/CN1026113C/zh

2005-08-20 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title description 2
ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 claims abstract description 31
238000000034 method Methods 0.000 claims abstract description 30
238000002360 preparation method Methods 0.000 claims abstract description 7
230000008569 process Effects 0.000 claims abstract description 7
-1 alkyl group glycosides Chemical class 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 10
125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 10
229930182470 glycoside Natural products 0.000 claims description 9
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
150000001241 acetals Chemical group 0.000 claims description 7
125000001931 aliphatic group Chemical group 0.000 claims description 5
239000007864 aqueous solution Substances 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 5
238000003786 synthesis reaction Methods 0.000 claims description 5
150000001720 carbohydrates Chemical class 0.000 claims description 4
239000002994 raw material Substances 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 3
239000003054 catalyst Substances 0.000 abstract description 15
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 12
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract description 7
239000007795 chemical reaction product Substances 0.000 abstract 1
239000000047 product Substances 0.000 description 12
239000002253 acid Substances 0.000 description 10
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 10
229960001031 glucose Drugs 0.000 description 10
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 9
239000008103 glucose Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
229920002472 Starch Polymers 0.000 description 7
LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical compound Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 description 7
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 7
235000019698 starch Nutrition 0.000 description 7
239000008107 starch Substances 0.000 description 7
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
150000002191 fatty alcohols Chemical class 0.000 description 6
150000004676 glycans Chemical class 0.000 description 5
239000000203 mixture Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 4
230000008901 benefit Effects 0.000 description 4
230000009466 transformation Effects 0.000 description 4
239000002585 base Substances 0.000 description 3
239000003925 fat Substances 0.000 description 3
229930182478 glucoside Natural products 0.000 description 3
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000011707 mineral Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
SPFMQWBKVUQXJV-BTVCFUMJSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;hydrate Chemical compound O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O SPFMQWBKVUQXJV-BTVCFUMJSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
239000004435 Oxo alcohol Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
238000007171 acid catalysis Methods 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
235000014633 carbohydrates Nutrition 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
208000012839 conversion disease Diseases 0.000 description 2
239000013078 crystal Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002338 glycosides Chemical class 0.000 description 2
PYIDGJJWBIBVIA-UYTYNIKBSA-N lauryl glucoside Chemical compound CCCCCCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PYIDGJJWBIBVIA-UYTYNIKBSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 2
PAEMERHSTIDLSE-QMCAAQAGSA-N (2r,3r,4s,5s,6r)-2-hexadecoxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound CCCCCCCCCCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PAEMERHSTIDLSE-QMCAAQAGSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
229930091371 Fructose Natural products 0.000 description 1
239000005715 Fructose Substances 0.000 description 1
208000007976 Ketosis Diseases 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
CYAYKKUWALRRPA-RGDJUOJXSA-N [(2r,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O CYAYKKUWALRRPA-RGDJUOJXSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001323 aldoses Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-PQMKYFCFSA-N alpha-D-mannose Chemical compound OC[C@H]1O[C@H](O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-PQMKYFCFSA-N 0.000 description 1
SRBFZHDQGSBBOR-QMKXCQHVSA-N alpha-L-arabinopyranose Chemical compound O[C@H]1CO[C@@H](O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-QMKXCQHVSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000003945 anionic surfactant Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000007857 degradation product Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
150000002028 dodecanols Chemical class 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
150000002584 ketoses Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
235000019600 saltiness Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000243 solution Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical class CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 1
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Biotechnology (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Crystallography & Structural Chemistry (AREA)
Saccharide Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Catalysts (AREA)

CN90107055.6A 1989-08-24 1990-08-20 烷基苷的制备方法 Expired - Fee Related CN1026113C (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP3927919.7		1989-08-24
DE3927919A DE3927919C2 (de)	1989-08-24	1989-08-24	Verfahren zur Herstellung von Alkylglykosiden

Publications (2)

Publication Number	Publication Date
CN1049667A CN1049667A (zh)	1991-03-06
CN1026113C true CN1026113C (zh)	1994-10-05

Family

ID=6387752

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN90107055.6A Expired - Fee Related CN1026113C (zh)	1989-08-24	1990-08-20	烷基苷的制备方法

Country Status (10)

Country	Link
US (1)	US5698684A (de)
EP (2)	EP0415192B1 (de)
JP (1)	JP2975429B2 (de)
CN (1)	CN1026113C (de)
AT (1)	ATE113602T1 (de)
DE (2)	DE3927919C2 (de)
DK (1)	DK0415192T3 (de)
ES (1)	ES2063214T3 (de)
MY (1)	MY106860A (de)
WO (1)	WO1991002742A1 (de)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4127231A1 (de) *	1991-08-16	1993-02-18	Henkel Kgaa	Neue alkyletherglycoside
EP0537820B1 (de) *	1991-10-08	1998-05-06	Akzo Nobel N.V.	Glycosiduronsäuren (Herstellungsverfahren)
DE4134707A1 (de) *	1991-10-21	1993-04-22	Henkel Kgaa	Verfahren zur herstellung hellfarbiger alkyloligoglycosid-pasten
DE4137636A1 (de) *	1991-11-15	1993-05-19	Henkel Kgaa	Verfahren zur herstellung von alkyl- und/oder alkenyloligoglycosiden
DE4212080A1 (de) *	1992-04-10	1993-10-14	Basf Ag	Verfahren zur Herstellung von Alkylglykosiden
DE4227752A1 (de) *	1992-08-21	1994-02-24	Basf Ag	Verfahren zur Herstellung von Alkylglykosiden
EP0615973A1 (de) *	1993-03-19	1994-09-21	Akzo Nobel N.V.	Verfahren zur Herstellung von Alkylglycosiden
FR2702769B1 (fr) *	1993-03-19	1995-06-16	Seppic Sa	Nouveau procede de preparation d'alkylpolyosides faiblement colores.
EP0617045A3 (de) *	1993-03-19	1998-05-13	Akzo Nobel N.V.	Verfahren zur kontinuierlichen Herstellung von Alkylglycosiden
US5478930A (en) *	1993-09-20	1995-12-26	Henkel Kommanditgesellschaft Auf Aktien	Process for producing light colored alkyl polyglucosides with partially sulfated fatty alcohol catalysts
DE19519384A1 (de) *	1995-05-26	1996-11-28	Henkel Kgaa	Verfahren zur Herstellung von Alkyloligoglucosiden mit hohem Oligomerisierungsgrad
CN1048253C (zh) *	1995-11-27	2000-01-12	河南开普化工股份有限公司	烷基糖苷合成新工艺
IT1295934B1 (it) *	1997-10-30	1999-05-28	Condea Augusta Spa	Procedimento migliorato per la sintesi di alchilpoliglucosidi
CN100390187C (zh) *	2005-12-02	2008-05-28	西北大学	一种制备烷基糖苷的方法
CA2691883A1 (en)	2007-07-06	2009-01-15	Basf Se	Method for the production of an aqueous glucose solution
DE102011102052A1 (de)	2011-05-19	2012-11-22	Anke Gmbh & Co. Kg	Netzmittel für elektrolytische Anwendung und dessen Verwendung
CN102643312A (zh) *	2012-04-23	2012-08-22	上海发凯化工有限公司	异构伯醇烷基糖苷及其合成方法与应用
EP4279495A1 (de) *	2022-05-20	2023-11-22	Basf Se	Verfahren zum herstellen von alkylpolyglycosid

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT135333B (de) *	1931-08-06	1933-11-10	H Th Boehme Ag	Verfahren zur Erhöhung der Kapillaraktivität.
US3598865A (en) *	1968-02-07	1971-08-10	Atlas Chem Ind	Polyglycosides and process of preparing mono and polyglycosides
US3547828A (en) *	1968-09-03	1970-12-15	Rohm & Haas	Alkyl oligosaccharides and their mixtures with alkyl glucosides and alkanols
US3839318A (en) *	1970-09-27	1974-10-01	Rohm & Haas	Process for preparation of alkyl glucosides and alkyl oligosaccharides
JPS6052689B2 (ja) *	1977-12-16	1985-11-20	ウェルファイド株式会社	アルキルフエノ−ル類の製造法
EP0132043B2 (de) *	1983-06-15	1994-08-31	THE PROCTER & GAMBLE COMPANY	Verfahren zur Herstellung von Alkyl-Glycoside
US4713447A (en) *	1983-06-30	1987-12-15	The Procter & Gamble Company	Process for preparing alkyl glycosides
US5003057A (en) *	1988-12-23	1991-03-26	Henkel Kommanditgesellschaft Auf Aktien	Process for production of glycosides

1989
- 1989-08-24 DE DE3927919A patent/DE3927919C2/de not_active Expired - Fee Related
1990
- 1990-08-16 EP EP90115694A patent/EP0415192B1/de not_active Expired - Lifetime
- 1990-08-16 DE DE59007615T patent/DE59007615D1/de not_active Expired - Lifetime
- 1990-08-16 AT AT90115694T patent/ATE113602T1/de not_active IP Right Cessation
- 1990-08-16 JP JP2512839A patent/JP2975429B2/ja not_active Expired - Lifetime
- 1990-08-16 ES ES90115694T patent/ES2063214T3/es not_active Expired - Lifetime
- 1990-08-16 WO PCT/EP1990/001349 patent/WO1991002742A1/de not_active Ceased
- 1990-08-16 EP EP90913819A patent/EP0489110A1/de active Pending
- 1990-08-16 US US07/835,447 patent/US5698684A/en not_active Expired - Lifetime
- 1990-08-16 DK DK90115694.3T patent/DK0415192T3/da active
- 1990-08-20 CN CN90107055.6A patent/CN1026113C/zh not_active Expired - Fee Related
- 1990-08-24 MY MYPI90001435A patent/MY106860A/en unknown

Also Published As

Publication number	Publication date
EP0415192A1 (de)	1991-03-06
US5698684A (en)	1997-12-16
ATE113602T1 (de)	1994-11-15
ES2063214T3 (es)	1995-01-01
DE3927919A1 (de)	1991-02-28
CN1049667A (zh)	1991-03-06
EP0489110A1 (de)	1992-06-10
DE3927919C2 (de)	2002-10-31
EP0415192B1 (de)	1994-11-02
JPH05500212A (ja)	1993-01-21
DK0415192T3 (da)	1995-02-27
JP2975429B2 (ja)	1999-11-10
DE59007615D1 (de)	1994-12-08
MY106860A (en)	1995-08-30
WO1991002742A1 (de)	1991-03-07

Legal Events

Date	Code	Title	Description
1991-03-06	C06	Publication
1991-03-06	PB01	Publication
1992-10-14	C10	Entry into substantive examination
1992-10-14	SE01	Entry into force of request for substantive examination
1994-10-05	C14	Grant of patent or utility model
1994-10-05	GR01	Patent grant
2002-04-24	C15	Extension of patent right duration from 15 to 20 years for appl. with date before 31.12.1992 and still valid on 11.12.2001 (patent law change 1993)
2002-04-24	OR01	Other related matters
2003-09-17	ASS	Succession or assignment of patent right	Owner name: KONIGSSEE GERMANY CO., LTD. AND LIMITED PARTNERSH Free format text: FORMER OWNER: HENKEL KOMMANDITGESELLSCHAFT AUF AKTIEN Effective date: 20030808
2003-09-17	C41	Transfer of patent application or patent right or utility model
2003-09-17	TR01	Transfer of patent right	Effective date of registration: 20030808 Patentee after: A nice Germany GmbH & Co. kg Patentee before: Henkel Kommanditgesellschaft auf Aktien
2004-10-20	C19	Lapse of patent right due to non-payment of the annual fee
2004-10-20	CF01	Termination of patent right due to non-payment of annual fee

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CN1049667A (zh)	1991-03-06	烷基苷的制备方法
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EP0092876B1 (de)	1986-10-01	Verfahren zur Herstellung von Alkylpolysacchariden
EP0132043B2 (de)	1994-08-31	Verfahren zur Herstellung von Alkyl-Glycoside
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US5480979A (en)	1996-01-02	Process for the production of alkyl and/or alkenyl oligoglycosides
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JPS62292789A (ja)	1987-12-19	アルキルオリゴグリコシドの製造方法
JPH0696587B2 (ja)	1994-11-30	ブチルオリゴグリコシドの製造方法
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